Azodyestuffs insoluble in water



Patented Jan. 5, 1937 AZODYESTUFFS INSOLUBLE IN WATER No Drawing. Application April 2, 1936, Serial No. 72,288. In Germany April 12, 1935 5 Claims. (Cl. 260-95) OFFICE Our present invention relates to new valuable azodyestuifs insoluble in water more particularly to those corresponding to the general formula:

II N wherein R stands for a radical of the benzene or naphthalene series.

The new dyestffs are suitable for the manufacture of valuable color lakes and yield when produced on the fiber Valuable dyeings and printings which are distinguished by an intense yellowish shade and by good fastness properties.

The elfect of the new dyestuffs is surprising as the isomeric dyestuffs containing the phenoxy group in the o-position relative to the alkylsulfone group instead of to the diazo group show inferior tinctorial properties.

In order to further illustrate our invention the following example is given, the parts being by weight and all temperatures in centigrade degrees. We wish it however to be understood that our invention is not limited to the particular products nor reaction conditions mentioned therein.

Example Boiled cotton yarn is impregnated in the usual manner in the following impregnating bath (a) and then developed in the following dyeing bath (b):

(a) impregnating bath 1 (2 hydroxy 3- naphthoylamino) 2 methyl-4-chlorobenzene grs 4 Turkey red oil of 50% strength cc 8 5 Caustic soda solution of 34 B cc 12 S o l u t i o n of formaldehyde of 30% strength cc 2 Boiling water cc 500 Made up with water to liter 1 (b) dyeing bath 3 grs. of Z-amino-4-propylsulfone-diphenyl ether of the formula: 15

are dissolved at room temperature in a mixture of 3.2 grs. of nitrosyl sulfuric acid and 5 grs. of concentrated sulfuric acid and the mixture is heated to C. for about 1 hour. When the diazo solution is diluted with ice-water to about 2 liters, 50 grs. of sodium chloride are added and the sulfuric acid is neutralized by means of sodium acetate.

Then the dye goods are rinsed, soaped in the hot, rinsed again and dried. In this manner a clear strong yellowish scarlet dyeing of very good fastness properties is obtained.

The 2 amino-4-propylsulfone-diphenyl-ether may be prepared as for example in the following manner:

4-chloro-l-propylsulfone-benzene is dissolved in concentrated sulfuric acid and nitrated with nitric acid. 25 parts of the 3-nitro-4-ch1oro-1- propylsulfone-benzene thus obtained are treated in the usual manner with 20 parts of potassium phenolate whereby the Z-nitroA-propylsulfonediphenyl-ether is obtained which is reduced to the 2-amino-4-propylsulfone-diphenyl-ether of the M. P. 125 C.

means;

of some tense yellowish shade and. by good fastness pros wherein R1 stands for a. radical of the benzene series containing at least one alkoxy group which dyestufis are suitable for the manufacture of valuable color lakes and yield when produced on the fiber valuable dyeings and printings which are distinguished by an intense yellowish shade and by good fastness properties.

70 wherein R stands for a radical of the group consisting of the radicals of the benzene and naphthalene series which dyestuffs are suitable for the manufacture of valuable color lakes and yield when produced on the fiber valuable dyeings 75 and printings which are distinguished by an infurther new dyestuffs: erties.

. 5 Diazo-compound of the base Gombmed g g gg g 521 3 naphthoyl Shade 17H: 0 l-chloro-l-aminobenzene Yellowish scarlet. 10 4-chloro2-methyl-1-aminobenzene Bright yellowish scarlet.

SOZOZHIS lTIHa I Z-naphthylamine Yellowish scarlet. i O1 O 4-chloro-1-aminobenzene Clear yellowish scarlet.

SOZCZH5 O Z-naphthylamine Yellowish scarlet.

4-chloro-l-aminobenzene Do. 20 80202115 w 2-methoxy-1-aminobenzene Scarlet. H30 0 2.5-dimethoxy-4-chloro-1-aminobenzene. Clear yellowish red.

| Aminobenzene Yellowish scarlet. O 4 chloro-1-aminobenzene Do.

2naphthy1amine Bright yellowish scarlet. SOICHT 2methoxy-l-aminobeuzene Yellowish scarlet. 3O

IIIHZ Aminobenzene Orange. 4.-chloro-1-aminob zene Yellowish scarlet. Cl- O 4-chloro-2-methyl-l-amino Do. 2-methoxy-l-aminobenzene Do. S 20s 1 4-methoxy-1-aminoh enzene. D o. 35

I Aminobenzene Do. 01- O 4.-chloro-l-aminobenzene Do. I-naphthylamine Do. 01 SO2CaH- 40 IIIHZ O 2.5-dimethoxy-4-chloro-1-aminobenzene..- Red.

S0204Hn 5-chloro2-methoxy-1-aminobenzene.i Yellowish scarlet. 01 Q 4-methoxy-3chloro-l-aminobenzene- Red orange.

S02C4H9 2 -meth0xy-1-aminobenzene Yellowish scarlet. H3000 2.5-dimethoxy-ai-chloro1-aminobenzene Scarlet.

SOzC4Hu 'r' We claim: 2. Azodyestuffs insoluble in water of the gen- 1. 'Azodyestuffs insoluble in water of the general formula: eral formula:

. Ill

N H by N OH OH CON H-R1 OONH-R 3 An azodyestufi insoluble in water of the which dyestufi dyes when prepared on the fiber formula: yellowish scarlet shades.

5 An azodyestufi insoluble in water of the 0- S O2CaH7 formula:

15 which dyestufi dyes when prepared on the fiber yellowish scarlet shades.

4. An azodyestufi insoluble in water of the C1 formula: OOH; 2O W W MH, 2

I which dyestufi dyes when prepared on the fiber I red shades. N WERNER ZERWECK.

NORBERT STEIGER. AUGUST MODERSOHN.

25 OH OCH;

0 ONH@ WERNER SCI-ILEIFENBAUM. 

